Chemiluminescent formulations containing an alkylsiloxane

ABSTRACT

1. A CHEMILUMINESCENT FRMULATION COMPRISING AN ALKYLSILOXANE AND A TETRAKIS(DISUBSTITUTED-AMINO)ETHYLENE.

- Patented Apr. 30, 1974 in -which the Rs which can be alike or different, are

3,808,139 straight or branched chain alkyl or cycloalkyl hydrocar- CH U SC T FORMULATIONS bon radicals of from 1-10 carbons each, preferably no CONTAINING AN ALKYLSILOXANE more than live carbons each, which can be joined pair- Everett M. Bens, China Lake, and Richard G. Broplry,

Ridgecrest, Calif., assignors to the United States of America as represented by the Secretary of the Navy wise on nitrogen to form 3-5 membered monoaza heterocycles and on two nitrogens to form 3-7 membered diaza N Dr F d s t. 30 1964 4 0 610 heterocycles. The first member of the series, namely, tetrao awmg 1 mg. Cok 3 No 0 kis(dimethylamino)ethylene can be prepared by the re- U.S. Cl. 252-1883 6 Cl i action of dimethylamine and chlorotrifluoroethylene, as

10 reported by Pruett et al., J. Am. Chem. Soc., 72 3646 (1950). Although tetrakis(dimethylamino)ethylene was the one used in this invention because it was commer- The invention herein described may be manufactured and used by or for the Government of the United States of America for governmental purposes without the pay- .1 ment of any royalties thereon or therefor. V clally available, other tetrak1s(d1subst1tuted am1no)ethylenes could be successfully used as the chemiluminescent fogrlliglgtrigsgsnt invention relates to new chemiluminescent composition. These include Much research and experimentation is taking place in tetreklsfN-pyrrohdmyl)ethylene, the area of luminescence. Various chemiluminescent com- P' 9 pounds have been made but because most are liquid, P l' e 9 their effectiveness is often dependent upon a carrier. Visl Y F Y q h m cosity changes of the carrier influence the controllability 2O titmkls(dllnethyl1mmmethyleneammo)ithylene and limit use; also, the life of the emission of light or and others. I

glow is influenced. The present invention is for a new The selected silicone and chemiluminescent compounds chemiluminescent formulation which has improved physare mixed together in an inert atmosphere at room ical characteristics over tho kno perature until homogeneity results. The formulation is It is an object of this invention to provide a chemiln. then stored in an air-tight container until used. When the minescent formulation which has controllable spreading material is left in the p air, the lllmilleseellee gradhar teri ti ually decreases to a very faint glow, therefore, care must Another object is to provide achemiluminescent ma-m. b3 ek n tq PI the formulation from react ng eleterial which has use as a weapons sight marker. meme, f W t Yet another object is to provide a chemiluminescent The fellewmg are representative examples of the pematerial which can be successfully used as a search and i rfa l'ml t l eXhlblted controlled P g rescue id, H on a Water surface, little viscosity change due to tem- Still another object isv to produce a chemiluminescent p l rehvafld: Continued light emission despite Occasional submergence ;in water. These examples better describe thetinvention but are not to be construed as limiting it.

EXAMPLE I formulation which can besp'read on water.

K fiirthe". object'isto rodu'cea chemiluminescen V material'fwhichfhas.continued emission of light both bove below the .surfa'ce of the water. f

yi h h 'ye I proportions of siloxanes asv .well.

cured under the tradename 813-30.,0-43325 gram samples as the variety of viscositles permit control of surface were applied to water and showgd the followigg spread: spreading, especially on the surface of water. Changes in X in one hour and 12 minutes. n x 11/23, in two the Proportion of Peraminoethylenes, or similar chemilu minutes andil% diameterrin two hours and minutes. minescent compounds, influence duration arid/or intensity 45 i I of light emission. A EXAMPLE v I The siloxanes used herein are compounds composed of Ingredlemsf v. Percent by Welght silicon and oxygen and usually contain carbon and hydro- Tftl'akls(d lf nethylammo)ethylene 60 gen, and having in theirmoleculesthe structural unit lgim ghy ih q e I R SiO in which R is=a member selected from the group m' j m dfffihisfformmafion consisting of 3, z s 2 4 C6H5, and the e, to a water" surface where it spread to a maximumdiam e phe he efi- The:Be -F9 1i i111 ter i lam i fllesr e ill-2. 2 amnsa p e. p e 16 e flu by the R group's and theextent l'nking I Qv Silicone gums and fluids havingpr'e do mo ular W ights, were .used- They, in

' -like mate al'sold unde *sold as Ingredientsr i t Percent by weight 0 Tetrakis(dimethylamino)ethylene 47 Methylvinylsilicone (SE-31) 53 The silicone used in this formulation is a gun; sold fin der the trade name SE-31. -A 0.2214 gramsample applied.

to water showed the following spread: /2" x l" in one minute; 78" x l" in 17 minutes; 1" x 1%" in one hour, 16 minutes and remained constant for at least three hours,

EXAMPLE V Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 50-93 Tetraethoxysilicone (RTV-602) 7-50 The silicone used above is sold under the trade name RVT-602. It was found that if too much of this'silicone material was mixed with the chemiluminescent ingredient a jelly-like material formed which did not spread readily.

EXAMPLE VI Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 47 Dimethylsilicone (Viscasil 100,000) 53 A .022 gram sample of this formulation when spread on water gave a /8" diameter area in minutes and the area remained constant thereafter.

EXAMPLE VII Percent by weight Ingredients:

Tetrakis(dimethylamino)ethylene 40 Dimethylsilicone (SE-) 30 Dimethylsilicone (Viscasil oil 10,000) 30 The SE-30 used is a gum and the Viscasil oil 10,000 is a high molecular weight material.

EXAMPLE VIII Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 47 Dimethylsilicone (SE-30) 53 The silicone used herein is a gum. A 0.908 gram sample applied on water gave the following spread: x Va" in two minutes; /5" x 1 in 26 minutes; and 1" diameter in one hour 25 minutes.

. EXAMPLE IX Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 47 Methylphenylsilicone (SF-1017) 53 Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 25 to Dimethylsilicone 40 to 3.- A chemiluminescent formulation comprising the following:

Ingredients: Percent by weight -Tetrakis(dimethylamino)ethylene 25 Methylsilicone 8.3 Dimethylsilicone 66.7

4. A chemiluminescent formulation comprising the following:

Ingredients: Percent by weight Tetrakis(dimethylamino)ethylene 50 to 93 Tetraethoxysilicone 7 to 50 5. A chemiluminescent formulation comprising tetrakis(dimethylamino)ethylene and methylvinylsilicone.

6 A chemiluminescent formulation comprising tetrakis(dimethylamino)ethylene and rncthylvinylsilicone.

References Cited UNITED STATES PATENTS 3/1966 Coffman et a1. 252-301.2 X

6/1966 Burzynski et al. 252301.2 X

STEPHEN J. LECHERT, JR., Primary Examiner US. Cl. X.R. 252301.2 

1. A CHEMILUMINESCENT FRMULATION COMPRISING AN ALKYLSILOXANE AND A TETRAKIS(DISUBSTITUTED-AMINO)ETHYLENE. 